6-O-benzyl-4-C-hydroxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone

Base Information

• Chemical Name: 6-O-benzyl-4-C-hydroxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone
• CAS No.: 188682-09-9
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.294
• Mol file: 188682-09-9.mol

Synonyms:6-O-benzyl-4-C-hydroxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone

Chemical Property of 6-O-benzyl-4-C-hydroxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-benzyl-4-C-hydroxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone

There total 3 articles about 6-O-benzyl-4-C-hydroxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Formic acid (R)-2-benzyloxy-1-((R)-2-formyl-5-oxo-tetrahydro-furan-2-yl)-ethyl ester → 6-O-benzyl-4-C-hydroxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone (188682-09-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃;

DOI:10.1016/j.ejmech.2003.10.006

Reference yield:

C18H22O6 (188682-04-4) → 6-O-benzyl-4-C-hydroxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone (188682-09-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Dowex H¹⁺ resin / tetrahydrofuran; H₂O / 24 h / Heating

2: sodium periodate / methanol; H₂O / 1 h / 20 °C

3: 5 g / sodium borohydride / methanol / 0 °C

With sodium tetrahydroborate; sodium periodate; Dowex H¹⁺ resin; In tetrahydrofuran; methanol; water;

DOI:10.1016/j.ejmech.2003.10.006

Reference yield:

(5S,6R,8S,9R)-6-Benzyloxymethyl-8,9-dihydroxy-1,7-dioxa-spiro[4.4]nonan-2-one → 6-O-benzyl-4-C-hydroxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone (188682-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium periodate / methanol; H₂O / 1 h / 20 °C

2: 5 g / sodium borohydride / methanol / 0 °C

With sodium tetrahydroborate; sodium periodate; In methanol; water;

DOI:10.1016/j.ejmech.2003.10.006

upstream raw materials:

C₁₈H₂₂O₆

Downstream raw materials:

5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone

5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(E)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone

5-O-acetyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone

5-O-acetyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(E)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone